tert-Butyl (3S)-4-{6-[(5-chloro-2-methoxypyridin-3-yl)amino]pyridin-3-yl}-3-methylpiperazine-1-carboxylate → (S)-5-Chloro-3-(5-(2-methylpiperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one

HRID 1185156Notes

Reaction equation

HRID 1185156 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C@@H:18]3[CH3:30])=[CH:13][CH:12]=2)[C:5]([O:8]C)=[N:6][CH:7]=1>O1CCOCC1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][C@@H:18]3[CH3:30])=[CH:15][N:16]=2)[C:5](=[O:8])[NH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86684013tert-Butyl (3S)-4-{6-[(5-chloro-2-methoxypyridin-3-yl)amino]pyridin-3-yl}-3-methylpiperazine-1-carboxylate

Product 1

HCID 86684014(S)-5-Chloro-3-(5-(2-methylpiperazin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-oneYield 201.2%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of 138a (1.0 g, 2.3 mmol) in dioxane/HCl (30 mL) was stirred at 100° C. for 2 h. It was then evaporated under reduced pressure to afford 138b (1.48 g, crude) as a yellow solid. MS-ESI: [M+H]+ 320.3

Workup

  1. customIt was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-d2923ff010e94ce896343e95747cafed
Source dataset
uspto-grants-2014_03
Patent number
US08669251B2

Reaction notes

Loading…